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Jumpstart your career in five hard lessons by Steve Tobak

Think you’ve got what it takes to become a hot-shot executive but your boss is holding you back. Or maybe you’re just sick and tired of working your butt off while everyone else gets ahead. Well, quit your whining and do something about it.

No, don’t get a self-help book; they’re mostly a waste of time. I’ve got a better idea. But, before we go any further, I need to say this: I’m no career guidance expert, I don’t have volumes of data, and I’m not here to sell you anything. On the other hand, I do have five hard-learned, real-life lessons from the trenches.

Learning these lessons enabled my success. Yeah, I know, I hate people who say that too, “I was a big success in [fill in the blank] and, if you buy my book, you can be a success too.” The only difference between them and me is that I’m not trying to sell you anything.

Will my lessons work for you or anyone else? Fair question. I have no idea. But I do think they’re fundamental and not the kind of stuff you’re likely to find hanging around a bookstore. These are not obvious “falling-off-a-log” lessons. I learned them through painful trial and error. Speaking of which, if you’d like to know whose advice you’re taking, just check out my bio.

If there’s an overriding message, it’s this: success isn’t easy and there are no formulas. Anyone who says otherwise just wants to sell you something. Everything you’re about to read is hard, but I don’t know of any workarounds. If there was an easier way, trust me, I’d have tried it. And, like anything significant in life, just reading it isn’t likely to help you much. But if it resonates with you, perhaps it will affect your behavior and then, the sky’s the limit.

Lesson 1: Get in the line of fire. Find a way to put yourself in a critical position on a program that can make or break the company. Take big risks, especially early in your career when it doesn’t matter so much. Stick your neck out and test your reach. Management will respect your willingness to put your butt on the line for the company. Don’t get hung up on winning. Whether the project succeeds or fails is secondary. Same goes for titles and compensation. Show your capability first. Then see Lesson 2.

Lesson 2: Actively manage your career. Rarely will anybody hand you a promotion. You have to negotiate for it, schmooze for it, and work your tail off for it. If somebody’s in your way, find a way around him. Sell yourself up the management chain or laterally if you have to. Find a mentor and follow his advice. If all that fails, start interviewing. You have to be willing to jump companies and even geographies if you have to. But don’t make a lateral move; go for the next level up. It’s easier than you think to get a promotion when you switch companies.

Lesson 3: Find your passion. Follow your instincts and listen to what people you trust tell you. If you’re open and honest, you will eventually find your passion. When you do, be willing to change careers if necessary. Have the guts to make a lateral move, or even take a step back, but only if necessary to find your raison d’être - what you were meant to do. That will always be your best chance path to success. I did this once in my career and it paid off big-time.

Lesson 4: The race to the top is a marathon. Most great careers are built and earned over time. Not only do you have to be smart, opportunistic, and lucky; you have to be willing to sacrifice and work long and hard to get to the top. It’s fine if you’re not willing to do that, but make sure it’s your decision and not somebody else’s. You don’t want to wake up one day and find that you’re bitter because you didn’t go for it.

Lesson 5: Be practical about your goals. Your risk profile changes over time. Be honest about where you are in your career timeline and choose jobs and companies accordingly. Consider early-stage startups when you’re young and have time to see enough of them through to ensure a return on your time investment. Remember, playing startups is like playing poker; they don’t all pay off. When you’re older, try late-stage private or undervalued public companies that can benefit from your experience.

I’ll leave you with some advice I learned long ago. Six simple words with potent meaning: “The only true success is happiness.” In case it’s not obvious, it means that if trying to get ahead stresses you out and makes you and everyone you love miserable; ask yourself why you’re doing it. The answer may inspire you to reconsider your life’s priorities.